EP1017358B1 - Reduction de la croissance de la pilosite - Google Patents

Reduction de la croissance de la pilosite Download PDF

Info

Publication number
EP1017358B1
EP1017358B1 EP98946113A EP98946113A EP1017358B1 EP 1017358 B1 EP1017358 B1 EP 1017358B1 EP 98946113 A EP98946113 A EP 98946113A EP 98946113 A EP98946113 A EP 98946113A EP 1017358 B1 EP1017358 B1 EP 1017358B1
Authority
EP
European Patent Office
Prior art keywords
aminoacyl
trna synthetase
inhibitor
amino
hair growth
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired - Lifetime
Application number
EP98946113A
Other languages
German (de)
English (en)
Other versions
EP1017358A1 (fr
Inventor
Joseph H. Handelman
James P. Henry
Gurpreet S. Ahluwalia
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Gillette Co LLC
Original Assignee
Gillette Co LLC
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Gillette Co LLC filed Critical Gillette Co LLC
Publication of EP1017358A1 publication Critical patent/EP1017358A1/fr
Application granted granted Critical
Publication of EP1017358B1 publication Critical patent/EP1017358B1/fr
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

Links

Classifications

    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/49—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
    • A61K8/494—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with more than one nitrogen as the only hetero atom
    • A61K8/4946—Imidazoles or their condensed derivatives, e.g. benzimidazoles
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/40—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
    • A61K8/44—Aminocarboxylic acids or derivatives thereof, e.g. aminocarboxylic acids containing sulfur; Salts; Esters or N-acylated derivatives thereof
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/40—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
    • A61K8/44—Aminocarboxylic acids or derivatives thereof, e.g. aminocarboxylic acids containing sulfur; Salts; Esters or N-acylated derivatives thereof
    • A61K8/447—Aminocarboxylic acids or derivatives thereof, e.g. aminocarboxylic acids containing sulfur; Salts; Esters or N-acylated derivatives thereof containing sulfur
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/49—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
    • A61K8/4906—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with one nitrogen as the only hetero atom
    • A61K8/4913—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with one nitrogen as the only hetero atom having five membered rings, e.g. pyrrolidone carboxylic acid
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q7/00—Preparations for affecting hair growth
    • A61Q7/02—Preparations for inhibiting or slowing hair growth
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
    • A61K2800/74—Biological properties of particular ingredients
    • A61K2800/78—Enzyme modulators, e.g. Enzyme agonists
    • A61K2800/782—Enzyme inhibitors; Enzyme antagonists

Definitions

  • the invention relates to reducing hair growth in mammals.
  • a main function of mammalian hair is to provide environmental protection. However, that function has largely been lost in humans, in whom hair is kept or removed from various parts of the body essentially for cosmetic reasons. For example, it is generally preferred to have hair on the scalp but not on the face.
  • Swiss Patent Publication 495750 describes the use of S-trityl-L-cysteine as an antiseborrheic hair treatment composition.
  • PCT Publication WO 97/22329 describes the use of cysteine or derivatives thereof for imparting body and volume to hair.
  • PCT Publication WO 97/19672 describes the use of an arginase inhibitor to reduce hair growth.
  • Aminoacyl-tRNA syntheses are a family of enzymes that are involved in cellular protein synthesis. In particular, the enzymes participate in the activation of amino acids and the subsequent linkage of the amino acids to corresponding tRNAs. There is at least one specific aminoacyl-tRNA synthetase and tRNA for each of the twenty natural amino acids that make up protein molecules. Aminoacyl tRNA synthetases are discussed, for example, in P. Schimmel (1987) Ann. Rev. Biochem. 56:125-158.
  • unwanted mammalian (including human) hair growth -- particularly androgen-stimulated hair growth -- can be reduced by applying to the skin a dermatogically acceptable composition including an inhibitor of an aminoacyl-tRNA synthetase in an amount effective to reduce hair growth.
  • the unwanted hair growth which is reduced may be normal hair growth, or hair growth that results from an abnormal or diseased condition.
  • aminoacyl-tRNA inhibitors include S-trityl-L-cysteine; L-asparaginamide; 4-aza-DL-leucine; DL-serine hydroxamate; proflavine (hemisulfate salt); L-isoleucinol; N-phenylglycine; L-leucinol; L-methioninol; phe-leu-amide; tyramine; 3,4-dehydro-DL-proline; S-carbamyl-L-cysteine; ⁇ -methyl-DL-methionine; chloro-L-alanine; cis-hydroxy proline; L-prolinol; L-histidonol; L-tryptophan hydroxamate; DL-4-thiaisoleucine; DL-amino- ⁇ -caprolactam; L-aspartic acid amide; DL- ⁇ -hydroxynorvaline; cis-4-fluoro-L-proline
  • aminoacyl-tRNA inhibitors are amino acid analogous and inhibit the specific aminoacyl-tRNA synthetase associated with the analogous amino acid, although a particular inhibitor may sometimes inhibit aminoacyl-tRNA synthetase associated with more than one amino acid.
  • inhibitor of [name of amino acid] aminoacyl-tRNA synthetase means a compound that inhibits at least the aminoacyl-tRNA associated with the amino acid.
  • the amino acid may be one of the 20 naturally occurring amino acids (e.g., leucine, serine, etc.), or some other amino acid.
  • aminoacyl-tRNA synthetase inhibitors and a “inhibitor of aminoacyl-tRNA synthetase” means a compound that inhibits one or more aminoacyl-tRNA synthetase.
  • the aminoacyl-tRNA synthetase inhibitor preferably is incorporated in a topical composition that includes a non-toxic dermatologically acceptable vehicle or carrier which is adapted to be spread upon the skin.
  • suitable vehicles are acetone, alcohols, or a cream, lotion, or gel which can effectively deliver the active compound.
  • a vehicle is disclosed in U.S. Pat. No. 5,648,394.
  • a penetration enhancer may be added to the vehicle to further enhance the effectiveness of the formulation.
  • the concentration of the inhibitor in the composition may be varied over a wide range up to a saturated solution, preferably from 0.1 % to 30% by weight or even more; the reduction of hair growth increases as the amount of inhibitor applied increases per unit area of skin.
  • the maximum amount effectively applied is limited only by the rate at which the inhibitor penetrates the skin.
  • the effective amounts may range, for example, from 10 to 3000 micrograms or more per square centimeter of skin.
  • a composition may include more than one aminoacyl-tRNA synthetase inhibitor.
  • the composition may include two inhibitors of an aminoacyl-tRNA synthetase associated with a particular amino acid, or may include an inhibitor of an aminoacyl-tRNA synthetase associated with a first amino acid and an inhibitor of an aminoacyl-tRNA synthetase associated with a second amino acid.
  • the composition optionally may also include other compounds that are known to reduce hair growth when applied topically.
  • the composition should be topically applied to a selected area of the body from which it is desired to reduce hair growth.
  • the composition can be applied to the face, particularly to the beard area of the face, i.e., the cheek, neck, upper lip, and chin.
  • the composition can also be applied to the legs, arms, torso or armpits.
  • the composition is particularly suitable for reducing the growth of unwanted hair in women suffering from hirsutism or other conditions.
  • the duration of treatment to achieve a perceived reduction in hair growth may vary depending upon, for example, the severity and location of the unwanted hair growth.
  • the composition for example, may be applied once or twice a day, or even more frequently, for two weeks to six months (e.g., three months) to achieve a perceived reduction in hair growth.
  • Reduction in hair growth is demonstrated when the frequency or hair removal is reduced, or the subject perceives less hair on the treated site, or quantitatively, when the weight of hair removed by shaving (i.e., hair mass) is reduced.
  • flank organs of each of a group of hamsters are shaved. To one organ of each animal 10 ⁇ l. of vehicle alone once a day is applied, while to the other organ of each animal an equal amount of vehicle containing a aminoacyl-tRNA inhibitor is applied.
  • the flank organs are shaved and the amount of recovered hair (hair mass) from each is weighed. Percent-reduction of hair growth is calculated by subtracting the hair mass (mg) value of the test compound treated side from the hair mass value of the vehicle treated side; the delta value obtained is then divided by the hair mass value of the vehicle treated side, and the resultant number is multiplied by 100.
  • compositions provide a reduction in hair growth of at least about 25%, more preferably at least about 50%, and most preferably at least about 60% when tested in the Golden Syrian hamster assay.
  • a number of compositions containing an aminoacyl-tRNA synthetase inhibitor were tested in the Golden Syrian hamster assay; the results are provided in Table 1:
  • a dose response study with S-trityl-L-cysteine indicates that increasing the concentration of the inhibitor in the composition resulted in increased hair growth reduction.
  • the results are shown in Table 2.
  • Dose response inhibition of hair growth by S-trityl-L-cysteine Compound Dose pH Treated (mg) Control (mg) %Inhibition S-trityl-L-cysteine 7.5% 6.5 0.35 ⁇ .10 1.64 ⁇ .14 80 ⁇ 6 S-trityl-L-cysteine 5% 6.5 0.90 ⁇ .17 1.95 ⁇ .35 56 ⁇ 6 S-trityl-L-cysteine 1% 5.5 0.88 ⁇ .10 1.10 ⁇ .15 35 ⁇ 9 Vehicle: 90% H 2 O, 6% dipropylene glycol, nd 4% ethanol
  • Leucine and serine tRNA synthetase were assayed with a pH 8.6 buffer and a MgCl 2 concentration of 8 mM.
  • the reaction mixture is mixed with the hair follicle extract so that the final assay volume is 100 ⁇ l. Typically, 90-95 ⁇ l of the reaction mixture was mixed with 5-10 ⁇ l of the hair follicles extract.
  • the reaction was carried out at 37°C for 60 minutes. The reaction was terminated by removing the reaction mixture and placing it on a piece of filter paper that had been soaked with 10% trichloroacetic acid. The filter paper was washed 3 times in 10% trichloroacetic acid and 3 times in 5% trichloroacetic acid. The filter paper was dried and the insoluble radioactivity, corresponding to the 14 C-aminoacyl-tRNA, was counted in a scintillation counter.

Landscapes

  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Birds (AREA)
  • Epidemiology (AREA)
  • Dermatology (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
  • Cosmetics (AREA)

Abstract

La croissance de la pilosité chez un mammifère est réduite par l'application d'un inhibiteur d'aminoacyl-ARNt synthétase sur la peau.

Claims (23)

  1. Méthode cosmétique de réduction de la pousse des poils des mammifères comprenant
       la sélection d'une zone de peau sur laquelle on désire réduire la pousse des poils et
       l'application, sur ladite zone de peau, d'une composition dermatologiquement acceptable comprenant un inhibiteur d'une aminoacyl-ARNt synthétase, en une quantité efficace pour réduire la pousse des poils.
  2. Méthode selon la revendication 1, dans laquelle ladite aminoacyl-ARNt synthétase comprend l'aminoacyl-ARNt synthétase de l'alanine, l'aminoacyl-ARNt synthétase de l'arginine, l'aminoacyl-ARNt synthétase de l'asparagine, l'aminoacyl-ARNt synthétase de l'acide aspartique, l'aminoacyl-ARNt synthétase de la cystéine, l'aminoacyl-ARNt synthétase de la glutamine, l'aminoacyl-ARNt synthétase de l'acide glutamique, l'aminoacyl-ARNt synthétase de la glycine, l'aminoacyl-ARNt synthétase de l'histidine, l'aminoacyl-ARNt synthétase de l'isoleucine, l'aminoacyl-ARNt synthétase de la leucine, l'aminoacyl-ARNt synthétase de la lysine, l'aminoacyl-ARNt synthétase de la méthionine, l'aminoacyl-ARNt synthétase de la phénylalanine, l'aminoacyl-ARNt synthétase de la proline, l'aminoacyl-ARNt synthétase de la sérine, l' aminoacyl-ARNt synthétase de la thréonine, l'aminoacyl-ARNt synthétase du tryptophane, l'aminoacyl-ARNt synthétase de la tyrosine et/ou l'aminoacyl-ARNt synthétase de la valine.
  3. Méthode selon la revendication 1, dans laquelle ledit inhibiteur comprend la S-trityl-L-cystéine, le L-asparaginamide, la 4-aza-DL-leucine, l'hydroxamate de la DL-sérine, la proflavine (sel hémisulfate), le L-isoleucinol, la N-phénylglycine, le L-leucinol, le L-méthioninol, le phe-leu-amide, la tyramine, le L-isoleucinol, la 3,4-déshydro-DL-proline, la S-carbamyl-L-cystéine, l'α-méthyl-DL-méthionine, la chloro-L-alanine, la cis-hydroxyproline, le L-prolinol, le t-histidonol, l'hydroxamate du L-tryptophane, la thioisoleucine, le DL-amino-ε-caprolactame, l'amide de l'acide L-aspartique et/ou la DL-β-hydroxynorvaline.
  4. Méthode selon la revendication 1, dans laquelle ledit inhibiteur est choisi dans le groupe constitué par la cis-4-fluoro-L-proline, l'α-méthyl-DL-histidine ; la N-formyl-L-histidine, l'acide L-2-amino-3-sulfamoylpropionique ; le β-hydroxamate de l'acide L-aspartique ; la β-cyano-L-alanine ; la sélénocystamine et l'amide de l'acide 4-amino-n-butyrique.
  5. Méthode selon la revendication 1, dans laquelle ledit inhibiteur est choisi dans le groupe constitué par la DL-5-hydroxylysine ; l'hydroxamate de L-lysine ; la 3-(N-phénylacétyl)amino-2,6-pipéridinedione (Antinéoplaston A 10) ; l'acide 4-amino-4-phosphonobutyrique ; l'éthionamide; le 1,2-diamino-3-(4-imidazolyl)propane (histidinamine) ; l'α-méthylhistidine ; la (S)-2-méthylbutylamine ; la L-O-méthylthréonine ; et la DL-armentomycine (acide 2-amino-4,4-dichlorobutyrique).
  6. Méthode selon la revendication 1, dans laquelle ledit inhibiteur est choisi dans le groupe constitué par la DL-3-déshydroarmentomycine ; la DL-3-hydroxyleucine ; la 5,5,5-trifluoro-DL-leucine ; la β-(3-aminocyclohexyl)-DL-alanine; la DL-p-chloroamphétamine ; l'acide trans-2,6-diaminohex-4-énoïque ; l'ester de méthyle de l'acide DL-2,6-diphtalimidocaproïque ; la DL-5-hydroxylysine ; l'hydroxamate de L-lysine et la DL-4-oxalysine.
  7. Méthode selon la revendication 1, dans laquelle ledit inhibiteur est choisi dans le groupe constitué par la DL-4-sélénalysine ; le L-méthioninamide; l'acide 2-amino-4-méthylhex-4-énoïque; le (1S,2S)-2-amino-1-phényl-1,3-propanediol ; la N-benzyl-D-amphétamine ; la N-benzyl-L-phénylalanine ; la N-benzyl-D-phényléthylamine; le 1,3-bis(acétoxy)-2-nitro-1-phénylpropane (fénitropan) ; et le 1,2-diamino-3-(2,6-dichlorophényl)propane.
  8. Méthode selon la revendication 1, dans laquelle ledit inhibiteur est choisi dans le groupe constitué par le 1,2-diamino-3-hydroxy-5-phénylpentane, le 1,2-diamino-3-phénylpropane; la N-(2,6-dichlorobenzylidène)-2-phényléthylamine ; la N-(2,6-dichlorobenzyl)-2-phényléthylamine) ; la N-(4-fluorobenzyl)-L-phénylalanine ; la DL-fluorophénylalanine ; le sulfate de 2-hydroxyéthyl-2-phénylammonium ; la méthyl-DL-phénylalanine ; le L-phénylalaninol et la L-α-phénylglycine.
  9. Méthode selon la revendication 1, dans laquelle ledit inhibiteur est choisi dans le groupe constitué par la DL-thréo-β-phénylsérine, la β-2-thiényl-DL-alanine, l'ester de cyclohexyle de la N-trifluoroacétyl-L-phénylalanine, l'oxalate de 2-aminométhyl-4-isopropyloxypyrrolidine ; la 2-aminométhylpyrrolidine; la L-4-thiaproline ; la N-benzyléthanolamine ; la N-(2,6-dichlorobenzyl)éthanolamine ; la N-(2,6-dichlorobenzylidène)-éthanolamine ; et la DL-β-hydroxyleucine.
  10. Méthode selon la revendication 1, dans laquelle ledit inhibiteur est choisi dans le groupe constitué par le 1,2-diamino-5-phényl-3-pentanol ; le DL-7-azatryptophane, le DL-fluorotryptophane ; la 5-hydroxytryptamine ; le L-5-hydroxytryptophane, la DL-α-méthyltryptamine ; le méthyl-DL-tryptophane ; la tryptamine, le DL-2-amino-1-(4-hydroxyphényl)-1-propanol ; et la DL-3-fluorotyrosine.
  11. Méthode selon la revendication 1, dans laquelle ledit inhibiteur est choisi dans le groupe constitué par la 3-iodo-L-tyrosine, la 3-nitro-L-tyrosine ; le L-tyrosinol•HCl; l'acide L-thréo-2-amino-3-chlorobutyrique ; l'hexafluoro-DL-valine ; la DL-norvaline ; la L-4-thialysine ; la DL-éthionine ; la N,N'-di-CBZ-L-lysine ; la DL-3-fluorophénylalanine ; la DL-4-fluorophénylalanine et la DL-3,4-dihydroxyphénylalanine.
  12. Méthode selon l'une quelconque des revendications précédentes, dans laquelle la concentration dudit inhibiteur dans ladite composition est entre 0,1 % et 30 %.
  13. Méthode selon l'une quelconque des revendications précédentes, dans laquelle la composition réduit la pousse des poils d'au moins 20 %, de préférence d'au moins 50 %, plus préférablement d'au moins 60 %, quand elle est testée dans le modèle du hamster syrien doré.
  14. Méthode selon l'une quelconque des revendications précédentes, dans laquelle l'inhibiteur est appliqué sur la peau en une quantité de 10 à 3000 microgrammes dudit inhibiteur par centimètre carré de peau.
  15. Méthode selon l'une quelconque des revendications précédentes, dans laquelle ledit mammifère représente un humain.
  16. Méthode selon la revendication 15, dans laquelle ladite zone de peau est sur le visage d'un humain, sur une jambe d'un humain, sur un bras d'un humain, sur une aisselle d'un humain ou sur le torse d'un humain.
  17. Méthode selon l'une quelconque des revendications précédentes, dans laquelle ladite pousse des poils est une pousse des poils stimulée par les androgènes.
  18. Utilisation d'un inhibiteur d'une aminoacyl-ARNt synthétase pour la préparation d'un médicament pour le traitement d'une femme souffrant d'hirsutisme.
  19. Méthode de production d'une composition pour l'inhibition de la pousse des poils des mammifères, comprenant la sélection d'un inhibiteur d'une aminoacyl-ARNt synthétase, et la combinaison dudit inhibiteur, en une quantité efficace pour réduire la pousse des poils, avec un véhicule ou un support non-toxique, dermatologiquement acceptable.
  20. Méthode selon la revendication 19, dans laquelle ledit véhicule ou support est adapté à l'étalement sur la peau d'un mammifère.
  21. Méthode selon la revendication 19 ou 20, dans laquelle une composition cosmétique est produite.
  22. Méthode selon la revendication 19, dans laquelle ledit inhibiteur est tel que défini dans l'une quelconque des revendications 3 à 11.
  23. Utilisation non-thérapeutique d'un inhibiteur d'une aminoacyl-ARNt synthétase pour la réduction de la pousse des poils.
EP98946113A 1997-09-22 1998-09-18 Reduction de la croissance de la pilosite Expired - Lifetime EP1017358B1 (fr)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US08/935,181 US5939458A (en) 1997-09-22 1997-09-22 Reduction of hair growth
US935181 1997-09-22
PCT/US1998/019521 WO1999015136A1 (fr) 1997-09-22 1998-09-18 Reduction de la croissance de la pilosite

Publications (2)

Publication Number Publication Date
EP1017358A1 EP1017358A1 (fr) 2000-07-12
EP1017358B1 true EP1017358B1 (fr) 2004-08-11

Family

ID=25466669

Family Applications (1)

Application Number Title Priority Date Filing Date
EP98946113A Expired - Lifetime EP1017358B1 (fr) 1997-09-22 1998-09-18 Reduction de la croissance de la pilosite

Country Status (10)

Country Link
US (1) US5939458A (fr)
EP (1) EP1017358B1 (fr)
AR (1) AR017132A1 (fr)
AU (1) AU9319798A (fr)
BR (1) BR9812369B1 (fr)
CA (1) CA2304807C (fr)
DE (1) DE69825607T2 (fr)
ES (1) ES2221992T3 (fr)
WO (1) WO1999015136A1 (fr)
ZA (1) ZA988641B (fr)

Families Citing this family (25)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP3973748B2 (ja) 1998-01-14 2007-09-12 花王株式会社 発毛抑制剤
US6971875B2 (en) * 1999-09-24 2005-12-06 Cao Group, Inc. Dental curing light
US6235737B1 (en) 2000-01-25 2001-05-22 Peter Styczynski Reduction of hair growth
US6299865B1 (en) 2000-05-02 2001-10-09 Peter Styczynski Reduction of hair growth
FR2813188B1 (fr) * 2000-08-25 2003-01-17 Sederma Sa Utilisation de la tyramine dans des compositions cosmetiques destinees a eclaicir la peau
JP2002201168A (ja) * 2000-12-28 2002-07-16 Kaken Pharmaceut Co Ltd シクロヘキサン誘導体
US7439271B2 (en) 2001-06-27 2008-10-21 The Gillette Company Reduction of hair growth
JP4759182B2 (ja) * 2001-08-03 2011-08-31 花王株式会社 水溶性ショウキョウエキス
US20030036561A1 (en) * 2001-08-10 2003-02-20 Peter Styczynski Reduction of hair growth
US7261878B2 (en) * 2001-08-10 2007-08-28 The Gillette Company Reduction of hair growth
US6743822B2 (en) 2001-08-10 2004-06-01 The Gillette Company Reduction of hair growth
US20040198821A1 (en) * 2002-01-29 2004-10-07 Hwang Cheng Shine Reduction of hair growth
US7160921B2 (en) * 2002-01-29 2007-01-09 The Gillette Company Reduction of hair growth
US20030199584A1 (en) * 2002-04-11 2003-10-23 Ahluwalia Gurpreet S. Reduction of hair growth
US20040141935A1 (en) * 2003-01-21 2004-07-22 Peter Styczynski Reduction of hair growth
US7015349B2 (en) * 2003-03-26 2006-03-21 The Gillette Company Reduction of hair growth
US20040224981A1 (en) * 2003-05-01 2004-11-11 Nebojsa Janjic Antibacterial methods and compositions
WO2005004984A1 (fr) * 2003-07-14 2005-01-20 Power Paper Ltd. Dispositif et procede permettant de traiter des troubles pilosebaces
US20050112075A1 (en) * 2003-11-25 2005-05-26 Hwang Cheng S. Reduction of hair growth
US20050249685A1 (en) * 2004-04-27 2005-11-10 Natalia Botchkareva Reduction of hair growth
CA2589875A1 (fr) * 2004-12-22 2006-06-29 The Gillette Company Reduction de la croissance des poils
MX2007007624A (es) * 2004-12-22 2007-08-03 Gillette Co Reduccion del crecimiento del pelo con inhibidores de survivina.
US7618956B2 (en) * 2005-05-31 2009-11-17 The Gillette Company Reduction of hair growth
US7727516B2 (en) * 2006-02-28 2010-06-01 The Procter & Gamble Company Reduction of hair growth
JP5395381B2 (ja) * 2008-08-05 2014-01-22 花王株式会社 抑毛剤

Family Cites Families (33)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB1051870A (fr) * 1964-01-29
US3426137A (en) * 1965-12-23 1969-02-04 Olin Mathieson Hair growth inhibiting by aminobenzophenones
US4161540A (en) * 1966-08-22 1979-07-17 Schering Corporation Antiandrogenic agents and methods for the treatment of androgen dependent disease states
GB1458349A (en) * 1972-12-05 1976-12-15 Sykora F Composition for and a process therewith of treating the hair and/or scalps of animals
US4039669A (en) * 1975-08-01 1977-08-02 Sterling Drug Inc. Composition for topical application and use thereof
US4139638A (en) * 1976-09-23 1979-02-13 Schering Corporation Methods for the treatment of hirsutism
FR2380775A1 (fr) * 1977-02-22 1978-09-15 Sederma Sarl Composition " apres-epilation " favorisant un ralentissement progressif de la repousse des poils
US4191775A (en) * 1977-12-15 1980-03-04 Imperial Chemical Industries Limited Amide derivatives
US4269831A (en) * 1979-05-09 1981-05-26 Sterling Drug Inc. Topical dermatological method of use of an androstenopyrazole
US4439432A (en) * 1982-03-22 1984-03-27 Peat Raymond F Treatment of progesterone deficiency and related conditions with a stable composition of progesterone and tocopherols
JP2519024B2 (ja) * 1982-06-07 1996-07-31 花王株式会社 毛髪化粧料
US4508714A (en) * 1983-11-14 1985-04-02 Tihomir Cecic Organic scalp lotion
US4885289A (en) * 1983-12-12 1989-12-05 Breuer Miklos M Alteration of character of male beard growth
US4720489A (en) * 1984-10-15 1988-01-19 Douglas Shander Hair growth modification with ornithine decarboxylase inhibitors
US4935231A (en) * 1985-08-28 1990-06-19 Repligen Corporation Use of thioredoxin, thioredoxin-derived, or thioredoxin-like dithiol peptides in hair care preparations
US5091171B2 (en) * 1986-12-23 1997-07-15 Tristrata Inc Amphoteric compositions and polymeric forms of alpha hydroxyacids and their therapeutic use
US5096911A (en) * 1990-06-25 1992-03-17 Ahluwalia Gurpreet S Alteration of rate and character of hair growth
DE69128034T2 (de) * 1990-08-14 1998-04-16 Handelman Joseph H Enzymatische änderung des haarwuchses
US5189212A (en) * 1990-09-07 1993-02-23 University Of Georgia Research Foundation, Inc. Triarylethylene carboxylic acids with estrogenic activity
US5095007A (en) * 1990-10-24 1992-03-10 Ahluwalia Gurpreet S Alteration of rate and character of hair growth
DE4038693A1 (de) * 1990-12-05 1992-06-11 Heverhagen Ulrich Mittel zum reduzieren des wachstums bzw. zum entfernen der haare am menschlichen koerper
US5143925A (en) * 1990-12-20 1992-09-01 Douglas Shander Alteration of rate and character of hair growth
GB9118866D0 (en) * 1991-09-04 1991-10-23 Unilever Plc Cosmetic composition
GB9118979D0 (en) * 1991-09-04 1991-10-23 Unilever Plc Cosmetic composition
US5364885A (en) * 1992-11-13 1994-11-15 Ahluwalia Gurpreet S Reduction of hair growth
US5411991A (en) * 1992-12-22 1995-05-02 Shander; Douglas Method of reducing hair growth employing sulfhydryl active compounds
US5648394A (en) * 1993-05-27 1997-07-15 Boxall; Brian Alfred Topical composition for inhibiting hair growth
US5474763A (en) * 1994-03-11 1995-12-12 Shander; Douglas Reduction of hair growth
US5455234A (en) * 1994-03-16 1995-10-03 Ahluwalia; Gurpreet S. Inhibition of hair growth
US5554608A (en) * 1994-09-28 1996-09-10 Ahluwalia; Gurpreet S. Inhibition of hair growth
US5728736A (en) * 1995-11-29 1998-03-17 Shander; Douglas Reduction of hair growth
GB9525775D0 (en) * 1995-12-16 1996-02-14 Unilever Plc Cosmetic hair treatment method
US5824657A (en) * 1997-03-18 1998-10-20 Cubist Pharmaceuticals, Inc. Aminoacyl sulfamides for the treatment of hyperproliferative disorders

Also Published As

Publication number Publication date
DE69825607T2 (de) 2005-08-04
AR017132A1 (es) 2001-08-22
US5939458A (en) 1999-08-17
CA2304807C (fr) 2002-05-28
CA2304807A1 (fr) 1999-04-01
ES2221992T3 (es) 2005-01-16
ZA988641B (en) 1999-03-23
DE69825607D1 (de) 2004-09-16
WO1999015136A1 (fr) 1999-04-01
BR9812369A (pt) 2000-09-19
AU9319798A (en) 1999-04-12
BR9812369B1 (pt) 2010-11-16
EP1017358A1 (fr) 2000-07-12

Similar Documents

Publication Publication Date Title
EP1017358B1 (fr) Reduction de la croissance de la pilosite
EP0750489B1 (fr) Inhibition de la pousse des poils
US5364885A (en) Reduction of hair growth
AU681776B2 (en) Inhibition of hair growth
CA2316826C (fr) Reduction de la croissance du systeme pileux
EP0863740B1 (fr) Reduction du developpement pileux
CA2163534C (fr) Inhibition de la croissance capillaire
CA2184170C (fr) Inhibition de la croissance capillaire
CA2347975C (fr) Reduction de la pousse des poils
US5444090A (en) Method of reducing the rate of hair growth
MXPA00002847A (en) Reduction of hair growth

Legal Events

Date Code Title Description
PUAI Public reference made under article 153(3) epc to a published international application that has entered the european phase

Free format text: ORIGINAL CODE: 0009012

17P Request for examination filed

Effective date: 20000417

AK Designated contracting states

Kind code of ref document: A1

Designated state(s): DE ES FR GB IT

RIN1 Information on inventor provided before grant (corrected)

Inventor name: AHLUWALIA, GURPREET, S.

Inventor name: HENRY, JAMES, P.

Inventor name: HANDELMAN, JOSEPH, H.

17Q First examination report despatched

Effective date: 20030508

GRAP Despatch of communication of intention to grant a patent

Free format text: ORIGINAL CODE: EPIDOSNIGR1

GRAS Grant fee paid

Free format text: ORIGINAL CODE: EPIDOSNIGR3

GRAA (expected) grant

Free format text: ORIGINAL CODE: 0009210

AK Designated contracting states

Kind code of ref document: B1

Designated state(s): DE ES FR GB IT

REG Reference to a national code

Ref country code: GB

Ref legal event code: FG4D

REF Corresponds to:

Ref document number: 69825607

Country of ref document: DE

Date of ref document: 20040916

Kind code of ref document: P

REG Reference to a national code

Ref country code: ES

Ref legal event code: FG2A

Ref document number: 2221992

Country of ref document: ES

Kind code of ref document: T3

ET Fr: translation filed
PLBE No opposition filed within time limit

Free format text: ORIGINAL CODE: 0009261

STAA Information on the status of an ep patent application or granted ep patent

Free format text: STATUS: NO OPPOSITION FILED WITHIN TIME LIMIT

26N No opposition filed

Effective date: 20050512

PGFP Annual fee paid to national office [announced via postgrant information from national office to epo]

Ref country code: ES

Payment date: 20110919

Year of fee payment: 14

Ref country code: FR

Payment date: 20110901

Year of fee payment: 14

PGFP Annual fee paid to national office [announced via postgrant information from national office to epo]

Ref country code: IT

Payment date: 20110920

Year of fee payment: 14

PGFP Annual fee paid to national office [announced via postgrant information from national office to epo]

Ref country code: GB

Payment date: 20120829

Year of fee payment: 15

PGFP Annual fee paid to national office [announced via postgrant information from national office to epo]

Ref country code: DE

Payment date: 20120928

Year of fee payment: 15

REG Reference to a national code

Ref country code: FR

Ref legal event code: ST

Effective date: 20130531

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: FR

Free format text: LAPSE BECAUSE OF NON-PAYMENT OF DUE FEES

Effective date: 20121001

Ref country code: IT

Free format text: LAPSE BECAUSE OF NON-PAYMENT OF DUE FEES

Effective date: 20120918

REG Reference to a national code

Ref country code: ES

Ref legal event code: FD2A

Effective date: 20131021

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: ES

Free format text: LAPSE BECAUSE OF NON-PAYMENT OF DUE FEES

Effective date: 20120919

REG Reference to a national code

Ref country code: DE

Ref legal event code: R119

Ref document number: 69825607

Country of ref document: DE

GBPC Gb: european patent ceased through non-payment of renewal fee

Effective date: 20130918

REG Reference to a national code

Ref country code: DE

Ref legal event code: R079

Ref document number: 69825607

Country of ref document: DE

Free format text: PREVIOUS MAIN CLASS: A61K0007060000

Ipc: A61K0008490000

REG Reference to a national code

Ref country code: DE

Ref legal event code: R119

Ref document number: 69825607

Country of ref document: DE

Effective date: 20140401

Ref country code: DE

Ref legal event code: R079

Ref document number: 69825607

Country of ref document: DE

Free format text: PREVIOUS MAIN CLASS: A61K0007060000

Ipc: A61K0008490000

Effective date: 20140613

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: GB

Free format text: LAPSE BECAUSE OF NON-PAYMENT OF DUE FEES

Effective date: 20130918

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: DE

Free format text: LAPSE BECAUSE OF NON-PAYMENT OF DUE FEES

Effective date: 20140401